#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017708.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017708
loop_
_publ_author_name
'Meng, Gao-Xiang'
'Yang, He-Lin'
'Cheng, Cui-Xia'
'Huang, Xin-Tang'
_publ_section_title
;
 Two-dimensional networks in 2-methylanilinium picrate and
 2,5-dichloroanilinium picrate
;
_journal_coeditor_code           GD3342
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o337
_journal_page_last               o340
_journal_paper_doi               10.1107/S0108270110020846
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H6 Cl2 N + , C6 H2 N3 O7 -'
_chemical_formula_moiety         'C6 H6 Cl2 N + , C6 H2 N3 O7 -'
_chemical_formula_sum            'C12 H8 Cl2 N4 O7'
_chemical_formula_weight         391.12
_chemical_name_systematic
;
2,5-dichloroanilinium picrate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.606(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.3288(18)
_cell_length_b                   23.372(10)
_cell_length_c                   15.292(6)
_cell_measurement_reflns_used    1754
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.24
_cell_volume                     1542.1(11)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3948
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.8396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.260
_refine_ls_abs_structure_details 'Flack (1983), with 1131 Bijvoet pairs'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0473P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                2362
_reflns_number_total             2666
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3342.cif
_cod_data_source_block           II
_cod_original_cell_volume        1542.2(11)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2017708
_cod_database_fobs_code          2017708
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9100(8) 0.77700(14) 0.7377(3) 0.0165(8) Uani d . 1 . .
C C2 0.7887(8) 0.74163(15) 0.7997(2) 0.0171(8) Uani d . 1 . .
C C3 0.8303(9) 0.68291(16) 0.7961(3) 0.0225(9) Uani d . 1 . .
H H3 0.7472 0.6590 0.8386 0.027 Uiso calc R 1 . .
C C4 0.9922(9) 0.65911(16) 0.7309(3) 0.0234(9) Uani d . 1 . .
H H4 1.0268 0.6190 0.7290 0.028 Uiso calc R 1 . .
C C5 1.1028(8) 0.69482(16) 0.6684(3) 0.0205(8) Uani d . 1 . .
C C6 1.0656(8) 0.75408(16) 0.6707(2) 0.0184(8) Uani d . 1 . .
H H6 1.1451 0.7779 0.6274 0.022 Uiso calc R 1 . .
C C7 0.3468(7) 0.93006(15) 0.6052(2) 0.0162(8) Uani d . 1 . .
C C8 0.4988(8) 0.93024(16) 0.5244(2) 0.0179(8) Uani d . 1 . .
C C9 0.4983(8) 0.97680(16) 0.4662(2) 0.0200(8) Uani d . 1 . .
H H9 0.5992 0.9738 0.4135 0.024 Uiso calc R 1 . .
C C10 0.3502(8) 1.02692(15) 0.4862(2) 0.0185(8) Uani d . 1 . .
C C11 0.2201(8) 1.03260(16) 0.5655(2) 0.0190(8) Uani d . 1 . .
H H11 0.1316 1.0680 0.5812 0.023 Uiso calc R 1 . .
C C12 0.2203(8) 0.98559(15) 0.6224(2) 0.0179(8) Uani d . 1 . .
Cl Cl1 0.59161(17) 0.77184(4) 0.88212(6) 0.0259(2) Uani d . 1 . .
Cl Cl2 1.29302(19) 0.66517(4) 0.58377(6) 0.0265(2) Uani d . 1 . .
N N1 0.8782(8) 0.83947(13) 0.7437(2) 0.0192(7) Uani d . 1 . .
H H1A 0.682(10) 0.8537(17) 0.713(3) 0.023 Uiso d . 1 . .
H H1B 1.030(9) 0.8585(18) 0.715(3) 0.023 Uiso d . 1 . .
H H1C 0.877(9) 0.8473(16) 0.801(3) 0.023 Uiso d . 1 . .
N N2 0.6617(7) 0.87856(14) 0.4985(2) 0.0234(7) Uani d . 1 . .
N N3 0.3329(8) 1.07506(13) 0.4235(2) 0.0223(7) Uani d . 1 . .
N N4 0.0810(7) 0.99458(13) 0.70586(19) 0.0204(7) Uani d . 1 . .
O O1 0.3370(5) 0.88725(10) 0.65767(17) 0.0219(6) Uani d . 1 . .
O O4 0.4978(6) 1.07395(12) 0.36204(18) 0.0308(7) Uani d . 1 . .
O O5 0.1505(6) 1.11432(12) 0.43352(17) 0.0276(6) Uani d . 1 . .
O O2 0.6101(8) 0.83209(13) 0.5327(2) 0.0437(8) Uani d . 1 . .
O O3 0.8421(7) 0.88452(12) 0.4424(2) 0.0352(8) Uani d . 1 . .
O O6 0.1278(8) 1.04068(13) 0.74530(19) 0.0421(8) Uani d . 1 . .
O O7 -0.0799(6) 0.95665(11) 0.7322(2) 0.0259(6) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 120.6(3) ?
C6 C1 N1 . . 119.1(4) ?
C2 C1 N1 . . 120.3(4) ?
C3 C2 C1 . . 120.3(4) ?
C3 C2 Cl1 . . 120.4(3) ?
C1 C2 Cl1 . . 119.3(3) ?
C4 C3 C2 . . 120.2(4) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 118.7(3) ?
C3 C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
C4 C5 C6 . . 122.3(4) ?
C4 C5 Cl2 . . 119.1(3) ?
C6 C5 Cl2 . . 118.6(3) ?
C1 C6 C5 . . 118.0(4) ?
C1 C6 H6 . . 121.0 ?
C5 C6 H6 . . 121.0 ?
O1 C7 C12 . . 123.7(3) ?
O1 C7 C8 . . 125.2(3) ?
C12 C7 C8 . . 111.1(3) ?
C9 C8 C7 . . 124.4(3) ?
C9 C8 N2 . . 116.3(3) ?
C7 C8 N2 . . 119.3(3) ?
C10 C9 C8 . . 119.6(3) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 120.3(3) ?
C9 C10 N3 . . 120.2(3) ?
C11 C10 N3 . . 119.6(3) ?
C10 C11 C12 . . 119.3(3) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C11 C12 C7 . . 125.0(3) ?
C11 C12 N4 . . 116.6(3) ?
C7 C12 N4 . . 118.4(3) ?
C1 N1 H1A . . 113(2) ?
C1 N1 H1B . . 112(3) ?
H1A N1 H1B . . 103(3) ?
C1 N1 H1C . . 106(2) ?
H1A N1 H1C . . 109(3) ?
H1B N1 H1C . . 115(4) ?
O3 N2 O2 . . 123.3(3) ?
O3 N2 C8 . . 116.5(3) ?
O2 N2 C8 . . 120.1(3) ?
O4 N3 O5 . . 122.2(3) ?
O4 N3 C10 . . 118.7(3) ?
O5 N3 C10 . . 119.2(3) ?
O7 N4 O6 . . 123.1(3) ?
O7 N4 C12 . . 118.0(3) ?
O6 N4 C12 . . 118.9(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.379(5) ?
C1 C2 . 1.392(5) ?
C1 N1 . 1.470(5) ?
C2 C3 . 1.386(5) ?
C2 Cl1 . 1.729(4) ?
C3 C4 . 1.381(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(5) ?
C5 Cl2 . 1.733(4) ?
C6 H6 . 0.9500 ?
C7 O1 . 1.286(4) ?
C7 C12 . 1.441(5) ?
C7 C8 . 1.446(5) ?
C8 C9 . 1.405(5) ?
C8 N2 . 1.469(5) ?
C9 C10 . 1.381(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.384(5) ?
C10 N3 . 1.477(5) ?
C11 C12 . 1.401(5) ?
C11 H11 . 0.9500 ?
C12 N4 . 1.469(5) ?
N1 H1A . 0.99(4) ?
N1 H1B . 0.93(4) ?
N1 H1C . 0.90(4) ?
N2 O3 . 1.213(4) ?
N2 O2 . 1.234(4) ?
N3 O4 . 1.225(4) ?
N3 O5 . 1.228(4) ?
N4 O7 . 1.216(4) ?
N4 O6 . 1.243(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 . 0.99(4) 1.83(4) 2.823(4) 174(3) yes
N1 H1B O1 1_655 0.93(4) 1.78(4) 2.709(4) 174(4) yes
N1 H1C O5 2_675 0.90(4) 2.43(4) 3.230(4) 148(3) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.7(5) ?
N1 C1 C2 C3 . . . . -177.3(3) ?
C6 C1 C2 Cl1 . . . . -179.4(3) ?
N1 C1 C2 Cl1 . . . . 1.7(5) ?
C1 C2 C3 C4 . . . . -0.1(5) ?
Cl1 C2 C3 C4 . . . . -179.0(3) ?
C2 C3 C4 C5 . . . . -1.8(5) ?
C3 C4 C5 C6 . . . . 2.2(5) ?
C3 C4 C5 Cl2 . . . . -177.5(3) ?
C2 C1 C6 C5 . . . . -1.4(5) ?
N1 C1 C6 C5 . . . . 177.6(3) ?
C4 C5 C6 C1 . . . . -0.6(5) ?
Cl2 C5 C6 C1 . . . . 179.1(3) ?
O1 C7 C8 C9 . . . . 177.7(3) ?
C12 C7 C8 C9 . . . . -5.5(5) ?
O1 C7 C8 N2 . . . . -1.0(5) ?
C12 C7 C8 N2 . . . . 175.8(3) ?
C7 C8 C9 C10 . . . . 1.3(5) ?
N2 C8 C9 C10 . . . . -179.9(3) ?
C8 C9 C10 C11 . . . . 4.1(5) ?
C8 C9 C10 N3 . . . . -176.6(3) ?
C9 C10 C11 C12 . . . . -4.6(5) ?
N3 C10 C11 C12 . . . . 176.1(3) ?
C10 C11 C12 C7 . . . . -0.2(5) ?
C10 C11 C12 N4 . . . . 179.5(3) ?
O1 C7 C12 C11 . . . . -178.2(3) ?
C8 C7 C12 C11 . . . . 5.0(5) ?
O1 C7 C12 N4 . . . . 2.1(5) ?
C8 C7 C12 N4 . . . . -174.8(3) ?
C9 C8 N2 O3 . . . . 17.5(4) ?
C7 C8 N2 O3 . . . . -163.7(3) ?
C9 C8 N2 O2 . . . . -161.8(3) ?
C7 C8 N2 O2 . . . . 17.0(5) ?
C9 C10 N3 O4 . . . . -13.3(5) ?
C11 C10 N3 O4 . . . . 166.0(3) ?
C9 C10 N3 O5 . . . . 165.5(3) ?
C11 C10 N3 O5 . . . . -15.2(5) ?
C11 C12 N4 O7 . . . . 138.9(3) ?
C7 C12 N4 O7 . . . . -41.3(4) ?
C11 C12 N4 O6 . . . . -39.8(4) ?
C7 C12 N4 O6 . . . . 140.0(3) ?
